Acetoxyacetyl chloride → N-[(1R,2S)-1-(3-ethylphenyl)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-2-hydroxy-acetamide

HRID 13029Notes

Reaction equation

HRID 13029 reaction equation
Cl.[CH2:2]([C:4]1[CH:5]=[C:6]([C@@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:19]=[CH:18]3)[C@@H:11]([NH2:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1)[CH3:3].C([O:34][CH2:35][C:36](Cl)=[O:37])(=O)C>>[CH2:2]([C:4]1[CH:5]=[C:6]([C@@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[N:19]=[CH:18]3)[C@@H:11]([NH:13][C:35](=[O:34])[CH2:36][OH:37])[CH3:12])[CH:7]=[CH:8][CH:9]=1)[CH3:3]

Participants

3

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 66812954(1R,2S)-1-(3-ethylphenyl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-amine hydrochloride

Product 1

HCID 25013991N-[(1R,2S)-1-(3-ethylphenyl)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-2-hydroxy-acetamide

Procedure

The title compound was prepared analogous to the method described in Example 21 starting from (1R,2S)-1-(3-ethylphenyl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-amine hydrochloride (22a) (50 mg, 0.12 mmol), and Acetoxyacetyl chloride (14 μL, 0.13 mmol).

Sources & evidence

ORD record
ord-ff77cdfaa03f4c9b8ad761fd2d95308f
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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